Yellow monoazo dyes and process of making them.



nMTED STATES I scan RUDOLF REYHER, 0F OFFENBACH-ON-THE-MAIN, GERMANY, ASSIGNOR TO CORPORA- TION 0F CHEMISCHE FABRIK, GRIESHEIM-ELEKTRON, 0F FRANKFORT-ON-THE- MAIN, GERMANY.

i ,osnsca.

No Drawing.

Specification of Letters Iatent.

Application filed May 22, 1913.

Serial No. 769,171.

To all whom it may concern:

Be it known that I, RUnoLr REYIIER, doctor of philosophy, chemist, and a subject of the Russian Emperor, and resident of Offenbach-on-the-Main, in the GrandDuchy of Hesse, Germany, with the post-office address Dreieichring No. 18, have invented new and useful Improvements in Yellow Mon'oazo Dyes and Processes of Making Them, of which the following is a specification.

My invention relates to the production of new yellow monoazo dyes, which are obtained by combining the diazo compound of 1. 2. 3-meta-Xylidin (CH :NH :CH -1 :2 :3) body with a 1-sulfoaryl-5-pyrazolone-3-carboxylic acid. Under the term adjacent meta-xylidin body I include 1. 2. 3-metaxylidin and its sulfonic acids. The dyestufi's, thus obtained, which have probably the formula wherein R means H, so,H, are, when dry, yellow to orange powders, easily soluble in water to an yellow solution, dyeing wool immensely beautiful greenish yellow shades of an excellent fastness to light and yielding upon reduction with stannous clilorid and hydrochloric acid a 1. 2. 3-meta-Xylidin body and a l-sulfoaryl-a -amino-pyrazol0ne-3-carboxylic acid. As such a l-sulfoaryl-5-pyrazolone-3-carboxylic acid, as is used, as aforesaid, for the production of the dyestuffs, can be employed each pyrazolonecarboxylic acid containing the sulfo group and a substitucnt such as CH Cl in ortho, meta or para position to N.

In practising the new process I may proceed as follows the parts being by weight:

Example: 20.1 parts of 1. 2. 3anctaxylidinl-snlfonic acid, obtained by suitonating the l. 2. 3-meta-xylidin with fuming sulfuric acid are diazolized in the usual manner. The solution thus obtained, is poured on stirring at 0-5 G. into a solution of 36.3 parts at the sodium silt oi? l-orthochloro meta sulfophcnyl 5 pyrazolono 3-carboxylic acid in about 500 parts oil. water and 19 parts of calcinated soda. When C33 coon is an orange powder, hardly soluble in alcohol, very easily soluble in water to a greenish yellow solution, in sulfuric acid to an yellow solution, dyeing wool immensely beautiful greenish yellow shades of an eX- ccllent fastness to light and yielding upon reduction with stannous cl lorid and hydrochloric acid 1. 2. 3-meta-xylidin--sulfonic acid and l-ortho-chloroncta-sulfophenyllamino-3-pyrazolonc-3carboxylic acid. In like manner the combination can be made with 1. 2. 3-mota-Xylidin or its 5-sulfonic acid, obtainable by baking 1. 2. iii-meta Xylidin with 1 molecule of sulfuric acid of 66 B6. at 200. instead of 1-ortho-ch]oro meta sulfophcnyl 5 pyrazolone 3 carboxylic acid 1-ortho-chlcropara-sulfophenyl-5pyrazolonc-3-carboxylic acid or 1- orth i-mcthyl--meta and parasulfophenylfi-pyrazolonc-Zl-carboxylic acid can be employcd, or also an other 1-sulfoaryl-5-pyrazolone-3-carboxylic acid.

Now what I claim and desire to secure by Lctlcrs Patent is tho Following;

1. Process of making yellow monoazo dyes. consisting in combining the diazo compound of l. 27 3-molaxylidin body with a l-sulfoaryl-i-pyrazolonc-S-carboxylic acid.

7 2. .\s new articles the monoazo dyes, obtained by combining the diazo compound of l. 2. i-mota-xylidin body with a l-sulfoaryl- Fi-pyrazolonci-carboxylic acid, which are, when dry, yellow to orange powders, easily soluble in water to a yellow solution, dyeing wool imnicnscly beautiful greenish yellow shades of an excellent fastncss to light and yielding upon reduction with stannous chlorid and hydrochloric acid 1. 2. S-metaxylidin body and a l-siilf0aryl-4-amino-5 1 yrazolono-3-carboxylic acid.

3. Process of making yellow monoazo Patented Jan. 13, 1914..

dyes, consisting in combinin the dune compound of 1. 2. 31neta-Xylinclin sulfonic acid with a 1-sulfoaryl-5-pyraZ0lone-3-carboXylic acid.

4- As new articles the monoazo dyes, obtained by combining the diazo compound of 1. 2. 3-meta-Xylidin sulfonic acid with a l-sul t'oaryl-5-pyrazolone 3 carboXylic acid, which are, when dry, yellow to orange powders, easily soluble in water to a yellow solution, dyeing wool immensely beautiful "greenish yellow shades of an excellent fastness to light and yielding upon reduction with Stnnnous chlorid and hydrochloric acid 1. 2. S-meta-xylidin sulfonic acid and a 1 sultoaryl-l-amino 5 pyrazolone 3 carboxylic acid.

5. Process of making yellow monoazo dyes, consisting in combining the diam compound of 1. 2. 3-nieta-xylidin sulfonic acid with a 1-sulfochloro-phenyl-5-pyraZ olone-3- carboxylic acid.

(3. As new articles the monoazo dyes, ob

tained by combining the diazo compound of 1. '2. 3- meta-xylidin sulfonic acid with a 1 -.sulfo -chlo ro-phenyl-5-pyraz0lone-3-carboxylic acid which are, when dry, yellow to orange powders, easily soluble in water to a yellow solution, dyeing -wool immensely beautiful greenish yellow shades of an excellent fastness to light and yielding upon reduction with stannous chlorid and hydrochloric acid 1. 2. B-meta-xylidin sulfonic acid and a 1-sulfo-chloro-phenyl-4-amino-5- pyrazolone-3-carb0xylie acid.

7. Process of making a yellow monoazo dye, consisting in combining the diazo compound of the 1. 2. 3n1eta-xylidin--sulfonic acid with 1 -ortho-chlo'ro-meta-sulfophenyl- -pyrazolone-3-carboxylic acid. 8. As a new article the monoazo dye obtained by combining the diazo compound of the 1. 2. 3 meta Xylidin L sulfonic acid with 1 -ortho chloro meta sulfophenyl- 5- pyrazolone-3-earboxylic acid, which is, when dry, an orange powder, hardly soluble in alcohol, very easily soluble in Water to a greenish yellow solution, in sulfuric acid to a yellow solution, dyeing wool .immensely beautiful greenish yellow shades of an excellent iastness to light and yielding upon reduction with stannous chlorid and hydrochloric acid 1. 9.. 3-meta-Xylidin-d-sulfonic acid and l-ortho-chloro-meta-sulfophenyliamino-5-pyrazolone-3-carb0Xylic acid.

In testimony, that I claim the foregoing as my invention, I have signed my name in presence of two witnesses, this th day of May 1913.

' RUDOLF REYHER.

lVitnesses 5 PETER LAU'rnNsoI-mls'em, Fm'rz Diison. 

